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Key West Homes For Sale on the Ocean Side of the Island. Oceanfront Homes

Total Listings 43
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$4,850,000
Key West
Old Town Unrecord   - MM: 1.00
5 Bed, 5 Baths, 3,148 SqFt Days Listed: 59
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Investment opportunity! Weekly rentals are allowed! Nestled within the highly sought-after Truman Annex in Old Town Key West, 202 Admirals Lane exudes coastal charm and luxury living at its finest. Boasting 5 bedrooms and 4 full bathrooms, this meticulously maintained residence showcases beautifully renovated bathrooms and a private pool oasis, offering an idyllic retreat for residents and vacationers alike. Situated nearby the iconic Duval Street and the tranquil expanse of Fort Zachary Taylor State Park, this home epitomizes the quintessential Key West lifestyle. Upon entering, youre greeted by an inviting main living area, adorned with French doors that effortlessly blur the lines between indoor and outdoor living. A sun-drenched sunroom, encased in glass doors, is the perfect setting for relaxation or entertainment year-round. Additional living spaces abound, including a bright and airy sitting room. The main floor is thoughtfully appointed with a convenient full bathroom, ensuring comfort and convenience for guests. The 2nd level offers 4 bedrooms and 3 full baths and the ensuite 3rd floor is great for guest . Included is a Truman Annex transient rental license allowing for weekly rentals, 202 Admirals Lane presents a lucrative investment opportunity as a successful vacation rental. Rare for Key West, this home features a coveted 2-car garage, providing secure parking and storage, a coveted amenity for sure. Offered turnkey, the residence comes complete with all furnishings and future reservations, promising a seamless transition for discerning buyers or investors seeking the ultimate Key West retreat.

$6,500,000
Key West
The Foundry   - MM: 1.00
3 Bed, 3 Baths, 4,200 SqFt Days Listed: 319
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

This distinguished estate, erected in 1904, proudly stands as the revered historic landmark known as Building 11, The Smithery within the esteemed confines of the Truman Annex--an exclusive gated community formerly part of the United States Naval Station, Key West. This exceptional offering epitomizes expert restoration, boasting lofty ceilings, majestic 22 brick exterior walls, and imposing wooden beams that seamlessly marry historic allure with contemporary finesse upon an expansive, idyllic plot. A quintet of majestic arched French doors adorns the facade, beckoning vistas of the verdant tropical surroundings. The ground level unfolds with sweeping travertine floors adorned with artisanal fixtures, housing a gracious great room with a bespoke bar, a gourmet kitchen, an elegant dining area, and additional living space. Nestled on this level, a guest suite seamlessly extends to the inviting poolside retreat, graced with a cascading waterfall and tranquil stone deck. Ascending to the upper level reveals an enchanting realm, where the primary and guest suites are interconnected by a captivating gallery bridge, each enveloped in luxurious amenities and adorned with custom built-ins, sumptuous hardwood flooring, and exquisite lighting fixtures. Lavish bathrooms, featuring opulent upgrades, adorn both wings, ensuring unparalleled comfort and refinement. Exquisitely maintained, this abode has garnered the admiration of a select few, its architectural brilliance cherished by those fortunate enough to experience its splendor. The expansive carport, a newly fashioned storage enclave echoing the original architectural charm--further enhances the allure of this hidden treasure. Nestled amidst illustrious neighbors, including Trumans Little White House this jewel epitomizes one of the most coveted addresses within the Florida Keys, offering a lifestyle of unrivaled sophistication and allure.

$18,500,000
Key West
Filer Boyle Subdivision   - MM: 1.00
5 Bed, 5 Baths, 4,008 SqFt Days Listed: 208
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Concrete

Discover the epitome of unique luxury in the Florida Keys with the REAL Southernmost House of the Continental United States of America, a property that perfectly blends history, elegance, and an unrivaled location. Positioned adjacent to the iconic Southernmost Point buoy, where the Atlantic Ocean meets the Gulf of Mexico, this concrete 4,008-square-foot home stands as a landmark at the southernmost edge of the Continental United States on a large 17,000 sq. ft. lot. This exceptional property is the beloved home of renowned and honored American Artist, SEWARD JOHNSON and his wife. Johnson is famous for his life size figurative sculptures which are exhibited in public spaces locally (Marilyn Monroe at our Tropic Cinema) and internationally. This multi-family designated home boasts five bedrooms and five and a half bathrooms. Enjoy the charm and elegance of a historic home with modern amenities. As you enter through the front door into a formal living room, you are transported back to the Hemingway era. The formal living room opens up to a Florida room with tropical vibes, and glass sliding doors lead to the pool area. The home also features sealed coral stone flooring. From the living room, an elevator leads to the upstairs primary bedroom and two guest bedrooms, surrounded by a large balcony with endless vistas over the property and the Atlantic Ocean.Enjoy swimming in a beautiful large 50 x 20 ft. pool and the spacious outdoor lounging area with Ocean breezes. Bird watching will be your new favorite pastime. With its unique location, this property offers unparalleled ocean views and proximity to all of Key Wests vibrant attractions. Southernmost Beach is on the on the same block, with its sandy beach and restaurant. The property is equipped with a coveted transient license, allowing for nightly rentals, making it a prime investment opportunity for vacation rentals or a lavish private residence. THE Southernmost House is a rare gem in the heart of Key West.

The information being provided by the Florida Keys MLS is exclusively for consumers' personal, non-commercial use, and it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. Data last updated on 01-30-2025.
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